(Invited) Synthesis, Structures, and Properties of Stacked Antiaromatic Porphyrins

Tuesday, 30 May 2017: 11:40
Churchill C1 (Hilton New Orleans Riverside)
H. Shinokubo (Graduate School of Engineering, Nagoya University)
The stacking of antiaromatic compounds has not been well investigated. Theoretical calculations have proposed that staking of two antiaromatic systems lead to three-dimensional aromaticity, which results from mutual interactions between frontier orbitals of each π-system. However, there has been no experimental support for this interesting prediction.

Norcorrole is a ring-contracted porphyrin, which shows distinct antiaromatic character. We have discovered that diphenylnorcorrole Ni(II) adopts a triple-decker π–π stacked structure in the solid state. A significant reduction of antiaromaticity of the norcorrole skeleton was observed.